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Issue 16, 2000
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Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds in the presence of reusable zeolites

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Abstract

Reactions of mono-substituted aromatics of moderate activity with bromine in the presence of stoichiometric amounts of zeolite NaY proceed in high yield and with high selectivity to the corresponding para-bromo products. The zeolites can easily be regenerated by heating and reused. Similar para-selectivity can be achieved in the case of toluene by use of tert-butyl hypobromite as reagent, zeolite HX as catalyst, and a solvent comprising a mixture of tetrachloromethane and diethyl ether. Radical bromination of ethyl 4-methylbenzoate using bromine in the presence of light is catalysed by various zeolites and affords a high yield of ethyl 4-(bromomethyl)benzoate but with no great improvement in selectivity for monobromination.

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Article information


Submitted
16 Mar 2000
Accepted
13 Jun 2000
First published
19 Jul 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2745-2752
Article type
Paper

Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds in the presence of reusable zeolites

K. Smith, G. A. El-Hiti, M. E. W. Hammond, D. Bahzad, Z. Li and C. Siquet, J. Chem. Soc., Perkin Trans. 1, 2000, 2745
DOI: 10.1039/B002157L

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